000158200 001__ 158200
000158200 005__ 20180913060136.0
000158200 0247_ $$2doi$$a10.1021/jo00125a026
000158200 037__ $$aARTICLE
000158200 245__ $$aA Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction
000158200 269__ $$a1995
000158200 260__ $$c1995
000158200 336__ $$aJournal Articles
000158200 500__ $$aCAN 123:228861
000158200 500__ $$a34-3
000158200 500__ $$aAmino Acids, Peptides, and Proteins
000158200 500__ $$aInstitut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
000158200 500__ $$aJournal
000158200 500__ $$a0022-3263
000158200 500__ $$awritten in English.
000158200 500__ $$a61036-62-2P (Teicoplanin) Role: PNU (Preparation, unclassified), PREP (Preparation) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions); 99-10-5 (3,5-Dihydroxybenzoic acid); 331-25-9 (3-Fluorophenylacetic acid); 18942-49-9; 36394-75-9; 53088-68-9 (Methyl 3-chlorophenylacetate); 56613-80-0 ((R)-Phenylglycinol); 64123-77-9 (Methyl 3-fluorophenylacetate); 147949-76-6 Role: RCT (Reactant), RACT (Reactant or reagent) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions); 2150-44-9P (Methyl 3,5-dihydroxybenzoate); 22908-28-7P; 22908-29-8P; 29640-98-0P; 29640-99-1P; 97522-06-0P; 163395-21-9P; 163395-22-0P; 163395-23-1P; 163395-24-2P; 163395-25-3P; 168292-12-4P; 168292-14-6P; 168292-15-7P; 168292-16-8P; 168292-17-9P; 168292-18-0P; 168292-20-4P; 168292-21-5P; 168292-22-6P; 169339-41-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions); 168292-11-3P; 168292-13-5P; 168292-19-1P Role: SPN (Synthetic preparation), PREP (Preparation) (a convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions)
000158200 520__ $$aAn intramol. SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles I and II (R = NH2, NO2) related to F-O-G ring of teicoplanin. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted arom. rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha -amino acid III, required for the synthesis of II, was prepd. via an asym. Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization. [on SciFinder (R)]
000158200 6531_ $$aSubstitution reaction (arom.
000158200 6531_ $$aintramol.
000158200 6531_ $$aa convergent synthesis of 14-membered ring analogs of the teicoplanin binding pocket via intramol. nucleophilic arom. substitution reactions)
000158200 6531_ $$ateicoplanin biaryl ether ring fragment; intramol nucleophilic arom substitution
000158200 700__ $$0244710$$aZhu, Jieping$$g206332
000158200 700__ $$aBeugelmans, Rene
000158200 700__ $$aBourdet, Sebastien
000158200 700__ $$aChastanet, Jacqueline
000158200 700__ $$aRoussi, George
000158200 773__ $$j60$$k20$$q6389-96$$tJournal of Organic Chemistry
000158200 909C0 $$0252341$$pLSPN$$xU12326
000158200 909CO $$ooai:infoscience.tind.io:158200$$pSB$$particle
000158200 937__ $$aEPFL-ARTICLE-158200
000158200 973__ $$aOTHER$$rREVIEWED$$sPUBLISHED
000158200 980__ $$aARTICLE